Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-8, in the reply filed on September 4, 2026 is acknowledged.
The requirement is still deemed proper and is therefore made FINAL.
Accordingly, claims 9-20 (method) are withdrawn from consideration as being directed to a non-elected invention.
Drawings
The drawings were received on November 21, 2023. These drawings are acceptable.
Claim Objections
Claims 1 and 8 are objected to because of the following informalities:
Claim 1
Line 6, please insert the word -- the -- before “CO”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 1, line 5.
Line 8, please insert the word -- the -- before “CO”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 1, line 5.
Line 9, please insert the word -- the -- before “MeOH”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 1, line 3.
Claim 8
Line 2, please insert the word -- the -- before the word “formaldehyde”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 1, line 3.
Line 3, please insert the word -- the -- before the word “formaldehyde”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 1, line 3.
Line 4, please insert the word -- the -- before the word “glycolaldehyde”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 8, line 3.
Line 5, please insert the word -- the -- before the word “formaldehyde”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 1, line 3.
Line 6, please insert the word -- the -- before the words “glycolic acid”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 8, line 5.
Line 7, please insert the word -- the -- before the word “methyl-2-hydroxyacetate”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology. See claim 8, line 6.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness
rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claim(s) 1-3 and 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sugano et al. (US Patent Application Publication No. 2018/0264429 A1) in view WO 2014/046798 (‘798).
Regarding claim 1, Sugano teaches a system (= a chemical reaction system) [page 1, [0002]], comprising:
• a split (= note that an ion exchange membrane may be provided at the pipe 51) [page 2, [0021]] electrochemical cell (= the electrochemical reaction device 1) [page 2, [0020]] comprising
(i) an anode half-cell (= a room 112) [page 2, [0021]] comprising an anode half-cell inlet (= a pipe 58 →) [page 4, [0052]], and an anode suitable for oxidizing MeOH to formaldehyde (= the anode 13 contains an oxidation catalyst) [page 3, [0037]]1 and
(ii) a cathode half-cell (= a room 111) [page 2, [0021]] comprising a cathode half-cell
outlet (= the pipe 52 →) [page 4, [0044]], and a cathode suitable for reducing CO2 (= the cathode 12 contains a reduction catalyst to generate the product A such as the carbon compound by the reduction reaction of carbon dioxide or the like) [page 3, [0035]] to CO (= the
examples of the product A may include carbon monoxide) [page 1, [0014]]; and
• a hydrogenation (= the reactants may contain at least one of hydrogen and oxygen) [page 3, [0041]] reactor (= the reactor 21) [page 3, [0041]] comprising
۰ a catalyst component suitable for converting CO to MeOH (= the reactor 21 chemically reacts reactants containing the product A in the reaction solution 212 by using a catalyst supplied to the reaction chamber 211 through a pipe 54) [page 4, [0044]]2,
۰ a reactor inlet (= the pipe 53 →) [page 4, [0044]], and
۰ a reactor outlet (= a pipe 55 →) [page 4, [0042]],
wherein the hydrogenation reactor (= the reactor 21) [page 3, [0041]] is fluidly coupled to the cathode half-cell (= the pipe 52 →) [page 4, [0044]] and the anode half-cell (= a pipe 58 →) [page 4, [0052]] such that fluid comprising CO (= the examples of the product A may include carbon monoxide) [page 1, [0014]] that exits the cathode half-cell outlet is delivered to the reactor inlet (= the pipe 52 →) [page 4, [0044]] and fluid comprising MeOH (= as other products, there can be cited alcohols such as methanol) [page 4, [0050]] that exits from the reactor outlet (= a pipe 55 →) [page 4, [0042]] is delivered to the anode half-cell inlet (= further, the remainder of the product solution 312 except at least a part of the product B1 may be supplied from the separation and recovery device 31 to the room 112 through a pipe 58) [page 4, [0052]; and Fig. 5:
PNG
media_image1.png
696
954
media_image1.png
Greyscale
].
Sugano does not explicitly teach the following:
a. Wherein the anode half-cell comprises an anode half-cell outlet.
Sugano teaches that an oxidation reaction part including the anode 13 and the room 112 is provided to oxidize water or the like to generate oxygen or the like (page 3, [0036]].
Like Sugano, WO ‘798 teaches anodes for oxidizing water generating oxygen (ρ [0056]).
Second product extractor 112 may extract the second product 115 from the second region 118. The extracted second product 115 may be presented through a port of the system 100 for
subsequent storage and /or consumption by other devices and/or processes (ρ [0015]).
It would have been obvious to a person having ordinary skill in the art before the
effective filing date of the claimed invention to modify the anode half-cell taught by Sugano
with wherein the anode half-cell comprises an anode half-cell outlet. The person with ordinary skill in the art would have been motivated to make this modification because extracting a product from the anode region through a port of the system would have made a product recoverable from that region as taught by WO ‘798 in [0015] and Fig. 1A.
b. Wherein the cathode half-cell comprises a cathode half-cell inlet.
Sugano teaches that the room 111 is provided to reduce carbon dioxide (page 3, [0034]).
WO ‘798 teaches that the alcohol source 104 and carbon dioxide source 106 may be configured to supply the carbon-based reactant and carbon dioxide separately or jointly (ρ [0031]).
It would have been obvious to a person having ordinary skill in the art before the
effective filing date of the claimed invention to modify the cathode half-cell taught by Sugano
with wherein the cathode half-cell comprises a cathode half-cell inlet. The person with ordinary skill in the art would have been motivated to make this modification because an inlet would have been a configuration for supplying carbon dioxide to the cathode region as taught by WO ‘798 in [0031] and Fig. 1A.
Regarding claim 2, Sugano teaches wherein the split electrochemical cell houses a
membrane that is positioned between the anode half-cell and the cathode half-cell (= note that
an ion exchange membrane may be provided at the pipe 51) [page 2, [0021]].
Regarding claim 3, Sugano wherein the anode and the cathode are provided as separate
electrodes (= a cathode 12, an anode 13) [page 2, [0020]].
Regarding claim 5, Sugano teaches wherein the anode half-cell comprises an anolyte (=
the room 112 is able to store an electrolytic solution 16) and the cathode half-cell comprises a
catholyte (= the room 111 is able to store an electrolytic solution 15) [page 2, [0021]].
II. Claim(s) 4 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sugano et al. (US Patent Application Publication No. 2018/0264429 A1) in view WO 2014/046798 (‘798) as applied to claims 1-3 and 5 above, and further in view of Olah et al. (US Patent Application Publication No. 2010/0193370 A1).
Regarding claim 4, Sugano and WO ‘798 teach the system of at least claims 1-3 and 5 as applied above. The references do not explicitly teach wherein the anode and the cathode are provided as a membrane electrode assembly.
Sugano teaches that an ion exchange membrane may be provided at the pipe 51 (page 2, [0021]).
Olah teaches electrochemically reducing the carbon dioxide in a divided electrochemical cell (page 6, [0047]).
In a divided electrochemical cell in which anode cell compartment and cathode cell compartment is separated by a membrane electrode assembly (MEA) consisting of anion conducting (such as OH-, HCo3- or CO32-) polymeric membrane firmly sandwiched between catalyst coated cathode (preferably gold deposited on conducting Toray carbon paper or cloth) and catalyst coated anode (Pt deposited on conducting Toray carbon paper or cloth), at a potential of ~ -3.0 V vs Ag/AgCl reference electrode, CO2 is reduced and water is electrolyzed at the cathode side to an optimal 1:2 mixture of CO and H2 suitable for methanol production. Pure oxygen is produced at the anode. The use of such membrane electrode assembly (MEA) separator ensures facile separation of cathode and anode products (ρ [0083]).
It would have been obvious to a person having ordinary skill in the art before the
effective filing date of the claimed invention to modify the anode and cathode taught by
Sugano with wherein the anode and the cathode are provided as a membrane electrode assembly. The person with ordinary skill in the art would have been motivated to make this modification because using a membrane electrode assembly (MEA) would have ensured facile separation of cathode and anode products as taught by Olah in [0083].
III. Claim(s) 6-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sugano et al. (US Patent Application Publication No. 2018/0264429 A1) in view WO 2014/046798 (‘798) as applied to claims 1-3 and 5 above, and further in view of Olah et al. (US Patent Application Publication No. 2010/0193370 A1), Spencer (“Hydroformylation of Formaldehyde Catalysed by Rhodium Complexes,” Journal of Organometallic Chemistry (1980), Vol. 194, Issue 1, pp. 113-123) and Faveere et al. (“Glycolaldehyde as a Bio-Based C2 Platform Chemical: Catalytic Reductive Amination of Vicinal Hydroxyl Aldehydes,” ACS Catalysis (2020 Jan 3), Vol. 10, No. 1, pp. 391-404).
Regarding claims 6-8, Sugano and WO ‘798 teach the system of at least claims 1-3 and 5 as applied above. The references do not explicitly teach wherein the system further comprises a further reactor fluidly coupled to the split electrochemical cell (claim 6); wherein the further reactor is fluidly coupled to the anode half-cell outlet such that fluid expelled from the anode half-cell outlet is delivered to an inlet of the further reactor (claim 7); and wherein the further reactor comprises:
(i) a catalyst that promotes hydroformylation of formaldehyde to glycolaldehyde;
(ii) a catalyst that promotes hydroformylation of formaldehyde to glycolaldehyde; and a
catalyst and a support material that promotes hydrogenation of glycolaldehyde to ethylene
glycol;
(iii) a catalyst that promotes carbonylation of formaldehyde to glycolic acid;
(iv) reagents that promote esterification of glycolic acid to methyl 2-hydroxyacetate;
(v) a catalyst and a support material that promotes hydrogenation of methyl 2-hydroxyacetate to ethylene glycol; or
(vi) any combination of two or more of (i)-(v) [claim 8].
Sugano teaches as other products, there can be cited aldehydes such as formaldehyde
and acetaldehyde) [page 4, [0050]].
WO ‘798 teaches that the second region 118 may co-produce formaldehyde 412 from methanol 404 reactant (ρ [0038]).
Olah teaches that a second product extractor 112 may extract the second product 115 from the second region 118. The extracted second product 115 may be presented through a port of the
system 100 for subsequent storage and /or consumption by other devices and/or processes (ρ [0015]).
Spencer teaches that the hydroformylation of formaldehyde to glycol aldehyde (OHCCH2OH) is catalysed by rhodium complexes (page 113, abstract).
Faveere teaches that:
Reductive amination of glycolaldehyde (GA), the smallest sugar molecule and obtainable from biomass, creates a versatile platform for ethylamine products, potentially replacing current pathways via toxic ethylene oxide and dichloroethane (page 391, abstract).
Glycolaldehyde (GA) is the smallest molecule in the homologous series of reducing
sugars and it may have great potential to act as a renewable and safer alternative for C2 amine
synthesis (pages 391-392, bridging paragraph).
It would have been obvious to a person having ordinary skill in the art before the
effective filing date of the claimed invention to modify the system taught by Sugano with
wherein the system further comprises a further reactor fluidly coupled to the split electrochemical cell; wherein the further reactor is fluidly coupled to the anode half-cell outlet such that fluid expelled from the anode half-cell outlet is delivered to an inlet of the further reactor; and wherein the further reactor comprises: (i) a catalyst that promotes hydroformylation of formaldehyde to glycolaldehyde; (ii) a catalyst that promotes
hydroformylation of formaldehyde to glycolaldehyde; and a catalyst and a support material that promotes hydrogenation of glycolaldehyde to ethylene glycol; (iii) a catalyst that promotes carbonylation of formaldehyde to glycolic acid; (iv) reagents that promote esterification of glycolic acid to methyl 2-hydroxyacetate; (v) a catalyst and a support material that promotes hydrogenation of methyl 2-hydroxyacetate to ethylene glycol; or (vi) any combination of two or
more of (i)-(v). The person with ordinary skill in the art would have been motivated to make this modification because formaldehyde produced at the anode region by oxidizing methanol as taught by WO ‘798 in [0038] can be presented through a port of the system for other processes as taught by Olah in [0015] wherein the hydroformylation of formaldehyde would have been catalysed by rhodium complexes to produce glycol aldehyde as taught by Spencer on page 113, abstract, where glycolaldehyde would have had potential to act as a renewable and safer alternative for C2 amine synthesis as taught by Faveere on pages 391-392, bridging paragraph.
Citations
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Motoshige et al. (US Patent Application Publication No. 2018/0257057 A1) is cited to teach that the reactor 13 can generate a product which includes a carbon compound C by a chemical reaction of reactants which include at least one of the carbon compound A and the carbon compound B, and hydrogen. The reactor 13 has a room storing the reactant, for example, and can generate the carbon compound C by a chemical reaction using a catalyst
introduced into the room (page 3, [0030]; and Fig. 3).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to EDNA WONG whose telephone number is (571) 272-1349. The examiner can normally be reached Monday-Friday, 7:00 AM- 3:30 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Luan Van can be reached at (571) 272-8521. The fax phone number for the
organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be
obtained from Patent Center. Unpublished application information in Patent Center is available
to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/EDNA WONG/Primary Examiner, Art Unit 1795
1 Functional claim language that is not limited to a specific structure covers all devices that are capable of performing the recited function (MPEP § 2114).
2 Functional claim language that is not limited to a specific structure covers all devices that are capable of performing the recited function (MPEP § 2114).
Prosecution Insights